Finding Destinations By Deals, Rather Than Deals By Destination

Prices to various cities from my home airports in NYC using Kayak Buzz.

I have a chronic itch for travel that constantly needs to be scratched. I have a decent income, but nothing that stands out; I am well within the ranks of the 99%. So, how do I afford to go out and see the world, albeit in tiny doses?

I talk a lot about various techniques that I have learned, as well as some that I’ve constructed on my own, in the Travel Hacking section of the site. I save money in all sorts of ways, sometimes succumbing to doing trivial chores to save a petty amount of dough which instead will go towards travel expenses. Several weekend nights per month, I will myself to stay in, saving cash that would have been spent on a night out, and trying to fix up my website instead; I kill two birds this way. But there is one method I use to see the world that keeps me traveling, and in a relatively economical manner. As the title states, I find locations by deals, rather than finding deals by location. What this means is that I have no clue where many of my next trips are going to take me. Basically, I find the cheapest places to go, and I go there.

Many of my friends pick a destination which they’d like to travel to, and set the tentative time for departure for several months down the line, focusing on saving to fund the adventure, making reservations at various accommodations, and planning the attractions to be seen. Actually, everyone I know uses this method, and they do so because this way is safe and makes sense financially. Also, vacations of this proportion usually require advance notice for days to be requested off work.

I used to do travel this way, but I found years going by with only one or two significant travel adventures in each one, with a few short weekend jaunts within the Northeastern U.S. I started to crave more such adventures, and a few years ago it awoke in me that long-dormant childhood dream of traveling the world endlessly. Weekend road trips to distant concert venues turned into coast-to-coast drives, but my real desire was to do more travel abroad.

Now, I leave one or two weekends per month, going to different countries, while managing to make it back to work on time Monday morning. So, back to the point: Instead of choosing a destination, I use tools on some travel search engines to help me find the cheapest flights anywhere from my local airports for the upcoming weekends. There are always deals, and some that would not have crossed my mind. Since I live in New York, these quick weekend jaunts allow me to go to places such as the Caribbean, Mexico, Canada, Central America, South America, and even some of the closer parts of Europe, like London or Glasgow. I choose flights for always less than $400, and I can expect to spend only about $500, total, for the entire weekend, including airfare, lodging, meals, and more.

While these trips drive up the cost average if calculated against number of days, I find it well worth it. I never go to relax, or at least not on these short jaunts, as they are usually more hectic than a weekend back in Brooklyn. Though 8 days to a place at once is cheaper than taking 4 separate trips to that destination for 2 days each, I am happy seeing the world in this way. I still give myself time to take a real “vacation” or two every year, and at those times I can enjoy a slower-paced immersion into a foreign culture.

My favorite tool to use to facilitate this kind of search is Kayak Buzz (now called Kayak Explore). On the main screen, you type in your home airport, then you can choose from several different ways to perform your search: You can search by ‘Lowest Fare’, though that doesn’t do much more than an ordinary flight search. No, the best option to use is the ‘Top 25 Cities’. Then, below that, you choose which set of cities it will search from; You can choose world cities, where it will find the 25 lowest fares from your airport in the world, or you can pick a specific region, where it will show you the 25 cheapest cities in that region to fly to. Select the dates: The first option is my favorite, the ‘Upcoming Weekends’ search, as it will show you the cheapest 25 cities in the region which you selected on weekends, which can be anytime from a Thursday through Monday. Or, you can just choose a specific upcoming month, and it will find the cheapest set of dates for you. The ‘Top 25’ is really great, and it is how I’ve been finding economical cities to visit, both maintaining my budget while sustaining my wanderlust.

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